Ethyl acetate hexane → HCID 22046522, compound

HRID 1830753Notes

Reaction equation

HRID 1830753 reaction equation
C[O:2][C:3]([CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:15][CH3:16])[CH2:6]1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].CCOC(C)=O.CCCCCC>CCOCC>[CH2:15]([N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:14][CH:5]([CH2:3][OH:2])[CH2:6]1)[CH3:16]

Participants

5

Reactant 3

HCID 21226206Ethyl acetate hexaneHCID 21226445Aluminium lithium hydrideHCID 67256908HCID 67256908, compound

Product 1

HCID 22046522HCID 22046522, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 1-Ethyl-1,2,3,4-tetrahydro-quinoline-3-carboxylic acid methyl ester (123 mg, 0.56 mmol) in 1.5 mL of Et2O at 0° C. under nitrogen. LAH (1M in Et2O) was added dropwise with vigorous gas evolution and a white precipitate formation. After 30 min., TLC in 3/7 EtOAc/hexane showed complete loss of s.m. and appearance of a clean lower rf spot. The reaction was carefully quenched with 15% NaOH (3 mL) and 3 mL of Et2O was added and the mixture stirred rapidly at RT for 15 min. The layers were separated and the aqueous layer extracted 1×10 mL with Et2O. The organics were combined, dried (MgSO4), filtered and concentrated to a clear oil corresponding to the desired alcohol (105 mg, 95%).

Workup

  1. customat 0° C.
  2. customThe reaction was carefully quenched with 15% NaOH (3 mL) and 3 mL of Et2O
  3. additionwas added
  4. customThe layers were separated
  5. extractionthe aqueous layer extracted 1×10 mL with Et2O
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated to a clear oil corresponding to the desired alcohol (105 mg, 95%)

Sources & evidence

ORD record
ord-2ea37147eadc456ba52bd66f42db9ce3
Source dataset
uspto-grants-2006_06
Patent number
US07067506B2

Reaction notes

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